Réaction #43641

Équation de réaction

Water

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-1-piperidinecarboxylate

sodium hydroxide

dimethyl sulphate

cis-4-tertbutoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester

→

title compound

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(methyloxy)-1-piperidinecarboxylate

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Extractionthe product was extracted with ethyl acetate (150 ml)
2. 2
   AutreThe organic phase was separated
3. 3
   Autredried
4. 4
   FiltrationFiltration and evaporation to dryness

Mode opératoire

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-1-piperidinecarboxylate (for a synthesis, see WO2004058144, Example 5 (b) cis-4-tertbutoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester, Enantiomer 1) (2.2 g, 6.28 mmol) in THF (12 ml) was treated with 50% sodium hydroxide solution (12 ml), benzyltriethylammonium chloride (0.04 g) and dimethyl sulphate (1.31 g, 10.43 mmol) and stirred at RT for 60 hours. Water (100 ml) was added and the product was extracted with ethyl acetate (150 ml). The organic phase was separated and dried. Filtration and evaporation to dryness gave the title compound (2.2 g).

Source